Triethylamine → 3-(5-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-one

HRID 399595

Reaction equation

HRID 399595 reaction equation
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([N:17]=[C:18]=[S:19])[CH:16]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:20])=[C:15]([N:17]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:18]2=[S:19])[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 189682093-(5-Chloro-2-methylphenyl)-1-methyl-2-thioxo-imidazolidin-4-oneYield 72.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of sarcosine ethyl ester hydrochloride (7.68 g), 5 -chloro-2-methylphenyl-isothiocyanate (9.18 g), triethyl amine (12 g) and chloroform (200 mL) was heated at reflux for 5 hours. The mixture was cooled to ambient temperature, washed with 1N HCl(2×200 ), then with water (200 mL) The organic phase was evaporated to dryness. The residue was crystallized from ethanol to give the tide compound (9.2 g) as a tan solid, m.p. 132°-134° C. Anal. Calcd. for C11H11 Cl N2O S: C, 51.87; H, 4.35; N,11.00. Found: C, 51.79; H, 4.12; N, 10.73. Mass spectrum (EI, M.+) m/z 254/256.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. washwashed with 1N HCl(2×200 )
  4. customwith water (200 mL) The organic phase was evaporated to dryness
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-e0a61f638d964b3fb6a7b8356074f46f
Source dataset
uspto-grants-1998_10
Patent number
US05821372

Linked notes

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